Chen Lin, Zhang Xiang, Shi Ke-Jin, Leng Hai-Jun, Li Qing-Zhu, Liu Yu, Li Jiang-Hong, Wang Qi-Wei, Li Jun-Long
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu 610052, China.
J Org Chem. 2020 Aug 7;85(15):9454-9463. doi: 10.1021/acs.joc.0c00957. Epub 2020 Jul 23.
Asymmetric construction of α-carbolinones with easily available starting materials has recently attracted considerable attention from the synthesis community, and the development of effective catalysis for this target is in great demand. Here, a bifunctional Brønsted base catalyzed asymmetric [3 + 3] cyclization of indolin-2-imines and α,β-unsaturated -acylated succinimides was developed by using the strategy of noncovalent bonding catalysis. With this organocatalytic protocol, a variety of tetrahydro-α-carbolinones bearing different substituents were synthesized with up to 99% yield and up to 96:4 er.
最近，利用易于获得的起始原料不对称构建α-咔啉酮引起了合成界的广泛关注，并且迫切需要开发针对该目标的有效催化方法。在此，通过非共价键催化策略，开发了一种双功能布朗斯特碱催化的吲哚-2-亚胺与α,β-不饱和酰化琥珀酰亚胺的不对称[3 + 3]环化反应。通过这种有机催化方法，合成了多种带有不同取代基的四氢-α-咔啉酮，产率高达99%，对映体过量率高达96:4。
